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Pricey Homes from the Country's Most Expensive Main Streets

Representative of ordinary, middle-class America, "Main Street" has become the rallying cry of protesters, but they would probably turn their ire on the millionaire denizens of at least five American Main Streets, if they saw the listing prices of these properties. The first comes from the Brooklyn neighborhood of Dumbo, where the penthouse at 1 Main Street is listed for a whopping $18M. Boasting jaw-dropping skyline views, 6,800-square-feet of interior space, glass elevator, transparent clock faces and 50-foot ceilings, the trophy penthouse is actually discounted from its original $25M asking price. Despite a visit from Bravo's Selling New York and serving as an Esquire showhouse, the property has failed to sell since hitting the market back in 2010.

↑ Fewer families are further from the popular conception of Main Street than the Gardiners of East Hampton. Owners of the 3,300-acre Gardiners Island for nearly 400 years, since the property was granted to the family by the King of England, the family also kept an estate on East Hampton's far-from-humble Main Street. Following the death of Robert David Lion Gardiner—who once famously declared: "We have always married into wealth. We've covered all our bets. We were on both sides of the Revolution, and both sides of the Civil War. The Gardiner family always came out on top."—the stone manor was put up for sale. Today listed for $26.5M, the ten bedroom, nine bathroom mansion presides over 5.5 prime acres and has recently been refurbished.

↑ Nantucket's historic Main Street has been home to impeccably-maintained million-dollar mansions for decades, so it surprised the Times to find 141 Main in a shoddy state in 2001. That very house has since been fully renovated and listed for $7.9M. The historic columned manse, known as the George C. Gardner House, dates to 1835 and sits on a half-acre lot, but lacks any view of the ocean. There is, however, a private swimming pool, which, according to the listing, could no longer be installed under Historic District regulations.

↑ The the primary thoroughfare in ludicrously-expensive downtown Aspen, Colo., Main Street is actually less expensive than some of the quieter side streets, but that doesn't keep this modern mixed-use building from asking close to $10M. That price includes two ground-floor retail spaces, three "employee housing units," and a spectacular 2,900-square-foot penthouse with three bedrooms, four baths, a pair of fireplaces, gym, wine room, and heated balconies for year-round use.

↑ Located just a block from the beach for much of its length, Main Street in Santa Monica, Calif. is home to some expensive beach houses, but few quite as expensive as this $5.75M gallery/residence. Originally listed back in 2011 for $6.75M, the oddly decorated pad is plenty spacious, but a failure to stage may be holding this place back. Highlights include high ceilings, a lushly-planted roof deck, and more than 7,000 square feet.